Winchester Homes with Garrison Style

Welcome to Winchester, a charming town located in Middlesex County, Massachusetts. Known for its picturesque streets, top-rated schools, and strong sense of community, Winchester offers a perfect blend of small-town charm and modern amenities.

One of the unique architectural styles you'll find in Winchester is the Garrison style homes. These homes are characterized by their two-story design, with the second story slightly overhanging the first, creating a distinctive look. Garrison homes often feature a central chimney, symmetrical facade, and a sense of timeless elegance.

Living in a Garrison style home in Winchester allows you to enjoy the classic New England architecture while benefiting from modern updates and conveniences. With spacious interiors, cozy fireplaces, and beautiful curb appeal, Garrison homes offer a perfect mix of historic charm and contemporary living.

Whether you're drawn to Winchester for its excellent schools, proximity to Boston, or tree-lined streets, this town has something to offer for everyone. Explore the unique Garrison style homes in Winchester and experience the beauty and character of this vibrant community.

Newest Winchester Homes with Garrison Style

$1,650,000

5 Beds ⋅ 4 Baths ⋅ 73573887 MLS

Expansive living and unparalleled curb appeal define this exceptional five-bedroom garrison colonial, ideally positioned near the natural beauty and extensive trails of the Fells Reservation. Set in the highly regarded Muraco Elementary School district, this spacious home offers an inviting blend of timeless architecture, thoughtful updates, and remarkable flexibility for today’s lifestyle. The sun-filled first floor features an open, seamless flow designed for both everyday living and effortless entertaining. A thoughtfully appointed eat-in kitchen with premium Sub-Zero and Fisher & Paykel appliances opens to the dining space, creating an ideal setting for gathering. A wood-burning fireplace anchors the living room where you can watch the world go by from the gorgeous picture window. A home office, mudroom, and powder room add functionality to this level. Upstairs, the generous primary suite includes a full bath and convenient laundry, with tree-top views from the Juliet balcony, complemented by four additional bedrooms and a family bath. A finished walk-up attic provides valuable storage and flexible bonus space, while the finished lower level adds a generous family room and several bonus spaces ideal for a second home office, playroom, media space, or additional recreation area, with kitchenette and full bath allowing for ADU possibilities. Outside, enjoy a truly private retreat with a fully fenced yard and pristine in-ground pool, offering exceptional space for outdoor living, entertaining, and relaxation. A two-car attached garage adds everyday convenience. With generous proportions throughout, multiple flexible spaces, an inviting open floor plan, and close proximity to the Fells Reservation, this Winchester Highlands property offers a rare opportunity to enjoy space, privacy, and sophisticated everyday living in one of Winchester’s desirable neighborhoods.

117 Highland, Winchester

Listing courtesy of Listing Agent: Dara Singleton from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

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